Additionally, this is not just limited to CT.

There is a $2500 limit ...you’re Referring to the 2016 de minimis safe harbor election taxpayers can take for the improvement of existing property that otherwise must be depreciated?

@Andy OdanoFinding GC's is difficult but can be controlled by only releasing funds based on completion of the work.

You're most likely limited to 75% LTV on a cash out refi, per Fannie Mae guidelines. 

As you may know, SF is a heavily rent controlled city.

but have to see a doc proving they have control of the property, especially when they want me to send them Earnest Money. 

I don't think your strategies work in the NYC and surrounding boroughs market, the price points are way out of control and if you are a newbie the sharks are already consuming all the market.

@Samantha Soto @Casey J Burkhead is correct.  1 policy listing 2 buildings is the correct way to set it up.If there is a limit to the # of rentals, then you are working with Personal insurance policies. 

Because of this limitation, the properties with ADUs in my area of investment are being comped at a discount compared to duplexes which seems reasonable because a duplex can be purchased by a house hacker or an off site RE investor but the ADU can only be purchased by a house hacker/home owner.Check this for your area. 

One last point: It is important to ask if they have any limitation on the amount of profit spread between the A-B and B-C transaction.